NPASS Compound

Structure

CID49422 OpenBabel06191715382D 29 31 0 0 1 0 0 0 0 0999 V2000 0.1293 5.3916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 3.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 4.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2308 3.6974 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 2 0 0 0 0 5 22 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 23 1 0 0 0 0 9 10 2 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 2 0 0 0 0 13 24 2 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 21 24 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 25 29 1 0 0 0 0 26 28 1 0 0 0 0 27 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.34
Volume:	465.419
LogP:	5.655
LogD:	5.405
LogS:	-6.554
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	4.596
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.737
MDCK Permeability:	2.709097316255793e-05
Pgp-inhibitor:	0.195
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	91.9623031616211%
Volume Distribution (VD):	2.06
Pgp-substrate:	1.1885349750518799%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.661
CYP2C19-inhibitor:	0.161
CYP2C19-substrate:	0.841
CYP2C9-inhibitor:	0.22
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.313
CYP3A4-inhibitor:	0.656
CYP3A4-substrate:	0.861

ADMET: Excretion

Clearance (CL):	2.169
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.846
Skin Sensitization:	0.086
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.484

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC49422

Natural Product ID:	NPC49422
*Common Name:**	(3E)-3-[(2E)-2-[1-[(E)-5,6-Dimethylhept-3-En-2-Yl]-7A-Methyl-2,3,3A,5,6,7-Hexahydro-1H-Inden-4-Ylidene]Ethylidene]-4-Methylidenecyclohexan-1-Ol
IUPAC Name:	(3E)-3-[(2E)-2-[1-[(E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
Synonyms:
Standard InCHIKey:	MECHNRXZTMCUDQ-ZJGOHBTISA-N
Standard InCHI:	InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13+
SMILES:	OC1CCC(=C)/C(=C/C=C/2CCCC3(C2CCC3C(/C=C/C(C(C)C)C)C)C)/C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1365846
PubChem CID:	5353610
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001460] Vitamin D and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[10336650]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679315]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252923]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[17624889]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611049]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18768384]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19476340]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21912858]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[22111577]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	flower	n.a.	PMID[22166201]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23790907]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24948953]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25564559]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29154541]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Potency	6

Activity Type	# Activity
Individual Protein	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	31622.8	nM	PMID[543807]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	21136.0	nM	PMID[543808]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	26608.6	nM	PMID[543808]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	19952.6	nM	PMID[543807]
NPT2	Others	Unspecified		Potency	=	35481.3	nM	PMID[543807]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC49422 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1076
0.2-0.3	7993
0.3-0.4	15607
0.4-0.5	8813
0.5-0.6	6200
0.6-0.7	2290
0.7-0.8	477
0.8-0.85	66
0.85-0.9	23
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC9161
0.9846	High Similarity	NPC167272
0.9846	High Similarity	NPC269877
0.9275	High Similarity	NPC27395
0.9275	High Similarity	NPC329090
0.9143	High Similarity	NPC319090
0.9143	High Similarity	NPC328104
0.9028	High Similarity	NPC18603
0.9028	High Similarity	NPC76931
0.9028	High Similarity	NPC307965
0.9014	High Similarity	NPC315261
0.875	High Similarity	NPC113733
0.8611	High Similarity	NPC136188
0.8611	High Similarity	NPC230301
0.8611	High Similarity	NPC471468
0.8611	High Similarity	NPC285893
0.8611	High Similarity	NPC304309
0.8611	High Similarity	NPC134847
0.8611	High Similarity	NPC28657
0.8611	High Similarity	NPC288035
0.8611	High Similarity	NPC22105
0.8611	High Similarity	NPC162742
0.8551	High Similarity	NPC160209
0.8533	High Similarity	NPC324772
0.8529	High Similarity	NPC149680
0.8493	Intermediate Similarity	NPC321381
0.8493	Intermediate Similarity	NPC300324
0.8493	Intermediate Similarity	NPC321016
0.8493	Intermediate Similarity	NPC134330
0.8493	Intermediate Similarity	NPC129165
0.8493	Intermediate Similarity	NPC240604
0.8493	Intermediate Similarity	NPC107059
0.8421	Intermediate Similarity	NPC320525
0.8378	Intermediate Similarity	NPC198968
0.8378	Intermediate Similarity	NPC34019
0.8378	Intermediate Similarity	NPC155986
0.8378	Intermediate Similarity	NPC318495
0.8356	Intermediate Similarity	NPC257347
0.8356	Intermediate Similarity	NPC141071
0.8356	Intermediate Similarity	NPC471723
0.8333	Intermediate Similarity	NPC68443
0.8333	Intermediate Similarity	NPC474140
0.831	Intermediate Similarity	NPC145498
0.8289	Intermediate Similarity	NPC241290
0.8289	Intermediate Similarity	NPC209944
0.8289	Intermediate Similarity	NPC164840
0.8289	Intermediate Similarity	NPC234193
0.8267	Intermediate Similarity	NPC87604
0.8267	Intermediate Similarity	NPC205455
0.8267	Intermediate Similarity	NPC473943
0.8267	Intermediate Similarity	NPC477522
0.8267	Intermediate Similarity	NPC474216
0.8267	Intermediate Similarity	NPC186191
0.8243	Intermediate Similarity	NPC189883
0.8243	Intermediate Similarity	NPC237460
0.8243	Intermediate Similarity	NPC247325
0.8243	Intermediate Similarity	NPC470362
0.8243	Intermediate Similarity	NPC244488
0.8205	Intermediate Similarity	NPC470384
0.8205	Intermediate Similarity	NPC320548
0.8194	Intermediate Similarity	NPC242001
0.8182	Intermediate Similarity	NPC264245
0.8182	Intermediate Similarity	NPC47761
0.8158	Intermediate Similarity	NPC81306
0.8158	Intermediate Similarity	NPC109546
0.8158	Intermediate Similarity	NPC28862
0.8158	Intermediate Similarity	NPC47982
0.8158	Intermediate Similarity	NPC328714
0.8158	Intermediate Similarity	NPC143182
0.8158	Intermediate Similarity	NPC84694
0.8116	Intermediate Similarity	NPC238352
0.8116	Intermediate Similarity	NPC477009
0.8101	Intermediate Similarity	NPC474493
0.8101	Intermediate Similarity	NPC238485
0.8082	Intermediate Similarity	NPC471799
0.8077	Intermediate Similarity	NPC49964
0.8077	Intermediate Similarity	NPC50964
0.8077	Intermediate Similarity	NPC201852
0.8056	Intermediate Similarity	NPC475728
0.8052	Intermediate Similarity	NPC26117
0.8028	Intermediate Similarity	NPC32055
0.8028	Intermediate Similarity	NPC208999
0.8026	Intermediate Similarity	NPC65897
0.8026	Intermediate Similarity	NPC138621
0.8026	Intermediate Similarity	NPC285761
0.8026	Intermediate Similarity	NPC318136
0.8026	Intermediate Similarity	NPC244385
0.8026	Intermediate Similarity	NPC302041
0.8026	Intermediate Similarity	NPC167037
0.8026	Intermediate Similarity	NPC477514
0.8026	Intermediate Similarity	NPC6978
0.8026	Intermediate Similarity	NPC85346
0.8026	Intermediate Similarity	NPC275910
0.8	Intermediate Similarity	NPC96319
0.8	Intermediate Similarity	NPC286669
0.8	Intermediate Similarity	NPC476039
0.8	Intermediate Similarity	NPC46160
0.8	Intermediate Similarity	NPC222366
0.8	Intermediate Similarity	NPC202642
0.7973	Intermediate Similarity	NPC471797
0.7973	Intermediate Similarity	NPC477138
0.7973	Intermediate Similarity	NPC469533
0.7973	Intermediate Similarity	NPC469593
0.7973	Intermediate Similarity	NPC243342
0.7973	Intermediate Similarity	NPC469534
0.7971	Intermediate Similarity	NPC225415
0.7971	Intermediate Similarity	NPC290367
0.7971	Intermediate Similarity	NPC309300
0.7949	Intermediate Similarity	NPC474531
0.7949	Intermediate Similarity	NPC470383
0.7949	Intermediate Similarity	NPC474752
0.7949	Intermediate Similarity	NPC7505
0.7949	Intermediate Similarity	NPC82986
0.7949	Intermediate Similarity	NPC474731
0.7949	Intermediate Similarity	NPC209620
0.7949	Intermediate Similarity	NPC474683
0.7949	Intermediate Similarity	NPC23852
0.7949	Intermediate Similarity	NPC474759
0.7941	Intermediate Similarity	NPC274704
0.7922	Intermediate Similarity	NPC1319
0.7922	Intermediate Similarity	NPC30986
0.7922	Intermediate Similarity	NPC80530
0.7922	Intermediate Similarity	NPC209430
0.7922	Intermediate Similarity	NPC273410
0.7895	Intermediate Similarity	NPC214570
0.7887	Intermediate Similarity	NPC45782
0.7887	Intermediate Similarity	NPC197805
0.7875	Intermediate Similarity	NPC231310
0.7875	Intermediate Similarity	NPC33913
0.7875	Intermediate Similarity	NPC205845
0.7867	Intermediate Similarity	NPC118508
0.7867	Intermediate Similarity	NPC171148
0.7867	Intermediate Similarity	NPC322353
0.7867	Intermediate Similarity	NPC291503
0.7867	Intermediate Similarity	NPC313179
0.7867	Intermediate Similarity	NPC121744
0.7867	Intermediate Similarity	NPC69383
0.7857	Intermediate Similarity	NPC19569
0.7848	Intermediate Similarity	NPC5985
0.7848	Intermediate Similarity	NPC189972
0.7848	Intermediate Similarity	NPC296701
0.7848	Intermediate Similarity	NPC20853
0.7848	Intermediate Similarity	NPC470614
0.7848	Intermediate Similarity	NPC218616
0.7848	Intermediate Similarity	NPC202389
0.7848	Intermediate Similarity	NPC101462
0.7848	Intermediate Similarity	NPC1272
0.7838	Intermediate Similarity	NPC182717
0.7826	Intermediate Similarity	NPC279200
0.7821	Intermediate Similarity	NPC236112
0.7821	Intermediate Similarity	NPC13554
0.7821	Intermediate Similarity	NPC236237
0.7821	Intermediate Similarity	NPC322313
0.7821	Intermediate Similarity	NPC102253
0.7794	Intermediate Similarity	NPC323153
0.7792	Intermediate Similarity	NPC312328
0.7778	Intermediate Similarity	NPC274448
0.7778	Intermediate Similarity	NPC157257
0.7778	Intermediate Similarity	NPC216460
0.7763	Intermediate Similarity	NPC73875
0.7763	Intermediate Similarity	NPC106432
0.775	Intermediate Similarity	NPC475789
0.775	Intermediate Similarity	NPC474634
0.775	Intermediate Similarity	NPC317458
0.775	Intermediate Similarity	NPC477818
0.7746	Intermediate Similarity	NPC250977
0.7733	Intermediate Similarity	NPC91858
0.7722	Intermediate Similarity	NPC6707
0.7711	Intermediate Similarity	NPC470542
0.7703	Intermediate Similarity	NPC167706
0.7703	Intermediate Similarity	NPC111234
0.7692	Intermediate Similarity	NPC472463
0.7683	Intermediate Similarity	NPC261266
0.7671	Intermediate Similarity	NPC476431
0.7662	Intermediate Similarity	NPC91594
0.7662	Intermediate Similarity	NPC471798
0.7654	Intermediate Similarity	NPC124172
0.7654	Intermediate Similarity	NPC59453
0.7654	Intermediate Similarity	NPC209802
0.7654	Intermediate Similarity	NPC475798
0.7654	Intermediate Similarity	NPC221758
0.7654	Intermediate Similarity	NPC127606
0.7654	Intermediate Similarity	NPC185568
0.7654	Intermediate Similarity	NPC472265
0.7654	Intermediate Similarity	NPC470077
0.7647	Intermediate Similarity	NPC5698
0.7639	Intermediate Similarity	NPC69649
0.7639	Intermediate Similarity	NPC114651
0.7639	Intermediate Similarity	NPC68703
0.7632	Intermediate Similarity	NPC66566
0.7632	Intermediate Similarity	NPC103822
0.7632	Intermediate Similarity	NPC477923
0.7625	Intermediate Similarity	NPC470049
0.7625	Intermediate Similarity	NPC87489
0.7625	Intermediate Similarity	NPC30166
0.7625	Intermediate Similarity	NPC248886
0.7606	Intermediate Similarity	NPC476737
0.7606	Intermediate Similarity	NPC163678
0.7606	Intermediate Similarity	NPC27243
0.76	Intermediate Similarity	NPC201373

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC49422 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1173
0.2-0.3	4511
0.3-0.4	2357
0.4-0.5	575
0.5-0.6	221
0.6-0.7	117
0.7-0.8	24
0.8-0.85	9
0.85-0.9	9
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7144	Approved
1.0	High Similarity	NPD7143	Approved
0.9848	High Similarity	NPD7151	Approved
0.9848	High Similarity	NPD7150	Approved
0.9848	High Similarity	NPD7152	Approved
0.9846	High Similarity	NPD6923	Approved
0.9846	High Similarity	NPD6922	Approved
0.9275	High Similarity	NPD6926	Approved
0.9275	High Similarity	NPD6924	Approved
0.9155	High Similarity	NPD6932	Approved
0.9028	High Similarity	NPD7145	Approved
0.9014	High Similarity	NPD6933	Approved
0.8889	High Similarity	NPD6925	Approved
0.8889	High Similarity	NPD5776	Phase 2
0.8784	High Similarity	NPD7514	Phase 3
0.8767	High Similarity	NPD7322	Clinical (unspecified phase)
0.8667	High Similarity	NPD6902	Approved
0.8649	High Similarity	NPD6929	Approved
0.8649	High Similarity	NPD6683	Phase 2
0.8611	High Similarity	NPD7339	Approved
0.8611	High Similarity	NPD6942	Approved
0.8533	High Similarity	NPD6931	Approved
0.8533	High Similarity	NPD6930	Phase 2
0.8533	High Similarity	NPD7332	Phase 2
0.8289	Intermediate Similarity	NPD7509	Discontinued
0.8205	Intermediate Similarity	NPD6695	Phase 3
0.8182	Intermediate Similarity	NPD6898	Phase 1
0.8101	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6893	Approved
0.8	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD4785	Approved
0.7973	Intermediate Similarity	NPD4784	Approved
0.7867	Intermediate Similarity	NPD8264	Approved
0.7821	Intermediate Similarity	NPD7525	Registered
0.7805	Intermediate Similarity	NPD7750	Discontinued
0.7805	Intermediate Similarity	NPD7524	Approved
0.7703	Intermediate Similarity	NPD4243	Approved
0.7654	Intermediate Similarity	NPD4786	Approved
0.7647	Intermediate Similarity	NPD7637	Suspended
0.7529	Intermediate Similarity	NPD7136	Phase 2
0.7442	Intermediate Similarity	NPD7087	Discontinued
0.7407	Intermediate Similarity	NPD3667	Approved
0.7262	Intermediate Similarity	NPD5279	Phase 3
0.7179	Intermediate Similarity	NPD5275	Approved
0.7179	Intermediate Similarity	NPD4190	Phase 3
0.7176	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6079	Approved
0.7037	Intermediate Similarity	NPD7645	Phase 2
0.7037	Intermediate Similarity	NPD4195	Approved
0.7024	Intermediate Similarity	NPD3666	Approved
0.7024	Intermediate Similarity	NPD3665	Phase 1
0.7024	Intermediate Similarity	NPD3133	Approved
0.7011	Intermediate Similarity	NPD5328	Approved
0.6957	Remote Similarity	NPD4219	Approved
0.6951	Remote Similarity	NPD4748	Discontinued
0.6914	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3618	Phase 1
0.6778	Remote Similarity	NPD6399	Phase 3
0.6747	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4732	Discontinued
0.6629	Remote Similarity	NPD4753	Phase 2
0.6628	Remote Similarity	NPD3668	Phase 3
0.6593	Remote Similarity	NPD4202	Approved
0.6588	Remote Similarity	NPD4221	Approved
0.6588	Remote Similarity	NPD4223	Phase 3
0.6559	Remote Similarity	NPD5222	Approved
0.6559	Remote Similarity	NPD5221	Approved
0.6559	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5329	Approved
0.6531	Remote Similarity	NPD7333	Discontinued
0.6517	Remote Similarity	NPD4518	Approved
0.6512	Remote Similarity	NPD4788	Approved
0.6512	Remote Similarity	NPD5332	Approved
0.6512	Remote Similarity	NPD5331	Approved
0.6512	Remote Similarity	NPD5362	Discontinued
0.6489	Remote Similarity	NPD5173	Approved
0.6486	Remote Similarity	NPD368	Approved
0.6484	Remote Similarity	NPD6411	Approved
0.6477	Remote Similarity	NPD4694	Approved
0.6477	Remote Similarity	NPD5280	Approved
0.6471	Remote Similarity	NPD4790	Discontinued
0.6452	Remote Similarity	NPD5210	Approved
0.6452	Remote Similarity	NPD4629	Approved
0.6437	Remote Similarity	NPD4197	Approved
0.642	Remote Similarity	NPD4687	Approved
0.642	Remote Similarity	NPD4058	Approved
0.642	Remote Similarity	NPD5733	Approved
0.6383	Remote Similarity	NPD4697	Phase 3
0.6375	Remote Similarity	NPD5276	Approved
0.6374	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6640	Phase 3
0.6354	Remote Similarity	NPD5286	Approved
0.6354	Remote Similarity	NPD5285	Approved
0.6354	Remote Similarity	NPD4696	Approved
0.6353	Remote Similarity	NPD4822	Approved
0.6353	Remote Similarity	NPD4820	Approved
0.6353	Remote Similarity	NPD4819	Approved
0.6353	Remote Similarity	NPD4821	Approved
0.6316	Remote Similarity	NPD6084	Phase 2
0.6316	Remote Similarity	NPD4755	Approved
0.6316	Remote Similarity	NPD6083	Phase 2
0.631	Remote Similarity	NPD4271	Approved
0.631	Remote Similarity	NPD4268	Approved
0.6304	Remote Similarity	NPD5284	Approved
0.6304	Remote Similarity	NPD5281	Approved
0.6292	Remote Similarity	NPD4689	Approved
0.6292	Remote Similarity	NPD6409	Approved
0.6292	Remote Similarity	NPD4688	Approved
0.6292	Remote Similarity	NPD5205	Approved
0.6292	Remote Similarity	NPD5330	Approved
0.6292	Remote Similarity	NPD4138	Approved
0.6292	Remote Similarity	NPD7334	Approved
0.6292	Remote Similarity	NPD6684	Approved
0.6292	Remote Similarity	NPD7521	Approved
0.6292	Remote Similarity	NPD7146	Approved
0.6292	Remote Similarity	NPD5690	Phase 2
0.6292	Remote Similarity	NPD4690	Approved
0.6292	Remote Similarity	NPD4693	Phase 3
0.6289	Remote Similarity	NPD5223	Approved
0.6279	Remote Similarity	NPD5369	Approved
0.6264	Remote Similarity	NPD6051	Approved
0.6264	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD4747	Approved
0.625	Remote Similarity	NPD5290	Discontinued
0.625	Remote Similarity	NPD7638	Approved
0.6224	Remote Similarity	NPD5211	Phase 2
0.6224	Remote Similarity	NPD5226	Approved
0.6224	Remote Similarity	NPD5224	Approved
0.6224	Remote Similarity	NPD5225	Approved
0.6224	Remote Similarity	NPD4633	Approved
0.6207	Remote Similarity	NPD4269	Approved
0.6207	Remote Similarity	NPD4270	Approved
0.6203	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4096	Approved
0.6186	Remote Similarity	NPD7639	Approved
0.6186	Remote Similarity	NPD4700	Approved
0.6186	Remote Similarity	NPD7640	Approved
0.6176	Remote Similarity	NPD8262	Approved
0.6163	Remote Similarity	NPD5368	Approved
0.6163	Remote Similarity	NPD4695	Discontinued
0.6163	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4252	Approved
0.6162	Remote Similarity	NPD5175	Approved
0.6162	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4722	Approved
0.6154	Remote Similarity	NPD5737	Approved
0.6154	Remote Similarity	NPD4723	Approved
0.6154	Remote Similarity	NPD6672	Approved
0.6129	Remote Similarity	NPD7515	Phase 2
0.6125	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4137	Phase 3
0.6118	Remote Similarity	NPD3617	Approved
0.6111	Remote Similarity	NPD342	Phase 1
0.61	Remote Similarity	NPD5141	Approved
0.6078	Remote Similarity	NPD6899	Approved
0.6078	Remote Similarity	NPD6881	Approved
0.6067	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5778	Approved
0.6064	Remote Similarity	NPD5779	Approved
0.6049	Remote Similarity	NPD4787	Phase 1
0.6049	Remote Similarity	NPD6939	Phase 2
0.6049	Remote Similarity	NPD4691	Approved
0.6049	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7128	Approved
0.604	Remote Similarity	NPD6675	Approved
0.604	Remote Similarity	NPD5739	Approved
0.604	Remote Similarity	NPD6402	Approved
0.6026	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6435	Approved
0.6022	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5363	Approved
0.6	Remote Similarity	NPD4754	Approved
0.598	Remote Similarity	NPD5697	Approved
0.5976	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7102	Approved
0.5962	Remote Similarity	NPD7290	Approved
0.5962	Remote Similarity	NPD6883	Approved
0.5957	Remote Similarity	NPD8035	Phase 2
0.5957	Remote Similarity	NPD8034	Phase 2
0.5955	Remote Similarity	NPD7154	Phase 3
0.5938	Remote Similarity	NPD5695	Phase 3
0.5934	Remote Similarity	NPD4623	Approved
0.5934	Remote Similarity	NPD4519	Discontinued
0.5934	Remote Similarity	NPD6098	Approved
0.5934	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5786	Approved
0.5922	Remote Similarity	NPD7320	Approved
0.5922	Remote Similarity	NPD6011	Approved
0.5922	Remote Similarity	NPD4729	Approved
0.5922	Remote Similarity	NPD4730	Approved
0.5922	Remote Similarity	NPD5168	Approved
0.5918	Remote Similarity	NPD4225	Approved
0.5918	Remote Similarity	NPD5696	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data